The Cunning Little Tailor
by midnightskull
Summary: In this take on the classic fairytale 'The Valiant Little Tailor,' Fergus Roderick MacLeod sets out into the world to make his fortune before his demon deal is up. Instead, he stumbles upon a village of hunters in desperate need of his trickery and wit. He bests demons, monsters, and hunters to win his prize: the mayor's only daughter.


The Cunning Little Tailor

Once upon a time in a little village in the Scottish countryside, lived a tailor. This tailor was an ordinary man, but he was not an honorable man. Many of the people in his village didn't like him. They thought he was weak and vile. While he enjoyed the company of women, the ladies of the village rarely enjoyed spending time with him.

So this tailor struck a deal with a crossroads demon. In exchange for his soul after ten years' time, he requested an additional three inches below the belt. The tailor agreed to the deal without a qualm, and carried on his way.

One morning roughly five years after he had made his deal, the tailor awoke to a woman shouting in the streets trying to sell her jam. The tailor bought three jars and used one for his breakfast. He worked as he ate, and as he worked, seven flies settled on his food. So he took his napkin and struck the bugs, killing all seven at once.

Impressed with his talent, the tailor spent the day bragging to the other villagers that he killed seven in one blow. By the next morning, the tailor decided to set out into the world and make a quick fortune before his time was up. If he could kill seven in one blow, there was no telling what else he might be able to do.

While he journeyed through the forest to the next town, he stumbled across a man.

"You must be a very foolish man to be wandering in these parts. Men who walk here don't leave alive." The man told the tailor.

But the tailor was not afraid. "I'll have you know that I killed seven one blow yesterday morning."

"Seven?" The man asked, truly impressed. He thought the tailor meant he had killed seven men yesterday morning. "Just who are you?"

"My name is Fergus."

"You're the bloke that sold his soul for an extra three inches? You will make an excellent demon." As the man spoke, his eyes flashed the typical demonic black.

The tailor still was not afraid. In his overconfidence, he continued to boast. "I'll make a better demon than you'll ever be."

"Is that so? Then perhaps you can tell me just what a demon is capable of." The demon cackled. He admired this tailor's arrogance.

However, this tailor had no idea what a demon was capable of. He did know that a person could make a deal with a demon for just about anything. After all, he had made a deal himself. So he answered the demon in the woods with confidence. "Demons are capable of anything so long as a deal is made."

The demon was impressed yet again. The little tailor was smarter than he appeared. "Then I suppose you could tell me what can harm demons?"

Again, the tailor had no idea what a demon was weak to. He wasn't a religious man nor did he pay attention in church where there would certainly would have been mention of demons. Though with his wit and overconfidence, he was willing to make an educated guess. "Demons are weak to anything they can't control."

The demon in the woods faltered. The little tailor that killed seven in one blow was clever. "You will in fact make a fine demon, Fergus."

The demon stepped aside and allowed the tailor to leave the woods unharmed. Upon reaching the edge of the woods, the tailor was confronted by a group of five men. One of the men tossed some water on the tailor's face. Seeing no flinch from the tailor, the man apologized.

"My apologies, sir. We've heard about these woods and intended to kill the demons that live here." The man explained to the tailor.

The tailor simply grinned. "Oh, the demons? I have already taken care of them. In fact, I killed seven in one blow yesterday morning."

The tailor was no fool. He knew how killing seven in one blow sounded to these men, which is why he left out the flies. The group of men were impressed with the little tailor.

"Seven? In one blow?" One of the men remarked.

"You should come back to our village with us. We could use a skilled man such as yourself." Another man told the tailor, who heartily agreed and followed the men back to their village.

Upon arriving in the village, the little tailor was led to the largest house, where he was introduced to the village's unofficial mayor.

"My name is John Winchester. I'm the leader of this village. Your name is?"

"Fergus MacLeod." The mayor and the tailor shook hands.

"Well, Fergus, my men tell me you killed seven in one blow - that's mighty impressive. Did you really clear the forest of all the demons?" The other men in the room were all equally impressed with the tailor.

"While I did kill seven in one blow, I don't believe I killed all of the demons in that forest."

"Then will you help us finish off those demons for good? They are moving too close to our village for comfort." The mayor asked.

The tailor wasn't one for offering help without something in return. He was a selfish and greedy man, unlike some of the kind men in the room. "If I do, what's in it for me?"

"You may have my daughter's hand in marriage. Surely any man as strong as yourself will make a fine husband for my young rose."

But the tailor was not yet satisfied. "I should like to see her first."

"Of course." The mayor sent his eldest son to fetch his little sister. When the boy returned, the mayor's daughter was with him. Her hair was the color of wood from a walnut tree and her eyes the color of toffee. Her fair skin rivaled that of any European princess and she carried herself as if she were one. "This is my daughter, Marian."

Marian smiled politely at the tailor who was watching her. "You sent for me, father?"

"This man is to be your husband should he rid the forest of demons."

Little Marian was not excited by the idea. She always knew that her father would marry her off to a hunter, but she didn't like the idea of being married off to a man she had only just met. But she was in no position to argue with the mayor. "It's a pleasure to meet you."

The tailor took her offered hand and planted a rough kiss on the tender skin across the back of her hand.

"When will you be ready to head into the woods?" The mayor asked his prospective son-in-law.

"As soon as possible." The tailor was eager to be done with the task and collect his reward.

"Very well. Take what weapons you like. My men will be waiting for you at the edge of the village."

So the tailor gathered weapons from the village's collection and headed back to the woods with the hunters. Amongst the hunters were the original five that discovered the tailor as well as the mayor's two sons.

They set out without a problem until they reached the spot where the tailor had met the one demon. When they began to stumble upons signs of a demon, the tailor halted the hunters.

"I shall go ahead alone. I will call back to you if I find the demons and need your help."

No one argued with him, and the tailor continued down the path following the demonic signs. When he at last came across them, the demons greeted him with smiles.

"If it isn't Fergus! What brings you back here, tailor?"

"There are hunters here to kill you. I will give you but one chance to leave and never come back." The tailor replied. But he wasn't about to let the demons go without earning something for himself. "However, I will only let you leave if I get something in return."

"What is it you wish?" One of the demons asked the tailor.

"Should I need assistance, you are all at my command."

"And if we decline?" In answer, the tailor flashed his small collection of demon-killing weapons. The small group of less than bright demons quickly agreed to his terms, then fled their meatsuits, leaving a pile of bodies behind. In order to fool the hunters, the tailor quickly killed each previously possessed human laying on the ground before him.

Upon returning to the group of hunters, the tailor announced that the deed was done and the forest was rid of demons. In triumph, they returned to the village.

However, the mayor was hesitant to reward the tailor. He did not believe that he could kill that group of demons without help. So before he allowed him to wed his daughter, the mayor requested the tailor help with a vampire bothering the locals.

So the tailor agreed grudgingly, still aching for his prize, and made his way to the abandoned house in the woods where the vampire had taken up residence. The tailor wasted no time in summoning a demon.

"What is it you require assistance with?"

"Go and kill the vampire in that house."

"And if I don't?"

"Then I shall kill you, slowly and painfully."

"Very well." So the demon went inside the house and not a minute later, the vampire was dead. The demon left again, and the tailor returned to the village with the vampire's head in hand.

Still, the mayor was reluctant to give the tailor his prize. So he tasked the tailor with killing a werewolf.

Again, the tailor made his way to the werewolf's hideout and summoned a demon.

"What is it you require assistance with?"

"Go and kill the werewolf in that cave."

"And if I don't?"

"Then I shall kill you, slowly and painfully."

"Very well." So the demon went inside the cave and not a minute later, the werewolf was dead. The demon left again, and the tailor returned to the village with the werewolf's head in hand.

This time, the mayor had no other tasks for the tailor to complete. At last, the tailor was able to collect his prize. The tailor and the mayor's daughter were soon wed and lived in a house of their own at the edge of the village.

One night, the mayor's daughter was not yet asleep when she heard the tailor muttering in his sleep.

"I will make a better demon than you. I will make a better demon than you." He muttered over and over in his sleep. The mayor's daughter was at once alarmed. She swiftly left the bedroom to fetch some chalk, which she used to draw a devil's trap beneath her bed. She had no holy water stored in her house and she dared not wake him. If he was a demon, she would know by morning.

When morning came, she found the tailor was nowhere in sight. If he had been a demon, he would not have been able to leave the bed. Still, she was not at ease. So she sought out her father.

"Father! The strangest thing occurred last night. In his sleep, my husband continued to mutter 'I will make a better demon than you.' I thought he might be a demon, so I drew a devil's trap beneath the bed, but it did not hold him."

"So then what are you concerned about?" The mayor asked.

"I am not sure, but he must have been saying those words for a reason. I do not believe he is who he says he is"

"Neither do I, dear Marian. I will send your brothers tonight. Leave your bedroom door cracked, and they will come and kill him."

The mayor's daughter quickly agreed, neither of them noticing the demon on the other side of the door who rushed to inform the tailor of what he had just heard.

"They mean to kill me? After all I have done for them? Very well. I shall show them just who I am."

That night, the mayor's daughter left the bedroom door cracked just as her father had told her. When she climbed into bed, she assumed her husband was fast asleep, for he was muttering the same statement as before: "I will make a better demon than you."

But when he heard the mayor's sons creeping through the doorway, the tailor muttered louder, saying: "I will make a better demon than you. I have killed seven in one blow. I killed a nest of demons singlehandedly. I have killed vampires and werewolves on my own, and I will kill you with ease should you challenge me."

The mayor's sons had heard his statements, and quickly left the tailor's house. While still feigning sleep, the tailor smiled.

Five years later, when the tailor's deal was about to come to an end, the mayor's daughter had given birth to a son, who was three by the time his father had to leave. On the day his deal was to end, the tailor packed a bag to give the illusion of travel.

He kissed his wife and son, saying: "I am going away for a while. I will be back one day soon and when I do, we will leave this place behind and begin a new life somewhere else."

The mayor's daughter excitedly agreed and bade him farewell.

It had only taken a month of Earth time for the tailor to become a demon and quickly rise through the ranks of demons, becoming the King of the Crossroads. After which, he returned to his human wife and son.

He instructed them to pack their things and leave them on their bed. Asking no questions, the mayor's daughter did as she was told, then met her husband. The demon picked up his son and held his wife close, taking them to a palace he had acquired through a deal.

It was there that they lived: Crowley, the King of the Crossroads, his wife Marian, and their son Gavin. It was there that they lived happily ever after.

* * *

 **I hope you enjoyed my attempt to write in Grimm Brothers style. Inspiration struck while I was reading my collection of Grimm fairytales the other week, and I couldn't resist writing this.**

 **There will be another fairytale 'special' for Rose and Crowley at some point, most likely for Chapter 40 of 'A Rose By Any Other Name.'**

 **If you have any requests for a story or a oneshot, don't hesitate to send them to me! I will gladly (attempt to) write it!**

 **I do not own The Valiant Little Tailor or Supernatural. I do, however, own Marian Rose Winchester and anything that isn't canon and/or widely accepted by the fandom.**


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